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Cheap flights from Boston (BOS) to Chicago (CHI)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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Cheap flights from Boston to Chicago in August , September 2026

21 Aug - 03 Sep $ 224.00
BOS
Boston
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
BOS
Boston
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31 Aug - 16 Sep $ 293.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
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22 Aug - 01 Sep $ 346.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
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Last minute flights from Boston to Chicago

20 Aug - 31 Aug $ 294.00
BOS
Boston
JetBlue Airways
1 STOPS
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
29 Aug - 31 Aug $ 332.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
21 Aug - 31 Aug $ 366.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
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One-way flights to Chicago from Boston

12:45 PM - 6:29 PM
Frontier Airlines
1 Stops
8h 14m
BOS - CHI
$ 126
Kiwi
Pick dates
11:05 AM - 11:05 AM
JetBlue Airways
0 Stops
2h 54m
BOS - CHI
$ 166
Kiwi
Pick dates
10:38 AM - 10:38 AM
United Airlines
0 Stops
2h 51m
BOS - CHI
$ 224
Kiwi
Pick dates

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.